LIQUID CRYSTAL COMPOSITION FOR DIMMING AND LIQUID CRYSTAL DIMMING DEVICE

Abstract

A liquid crystal composition for dimming that satisfies at least one of characteristics such as a high maximum temperature, a low minimum temperature, a small viscosity, a large optical anisotropy and a large positive dielectric anisotropy, or that is suitably balanced between at least two of these characteristics, and a liquid crystal dimming device including this composition. A liquid crystal composition for dimming that includes a specific compound having a large positive dielectric anisotropy as a first component and that may include a specific compound having a high maximum temperature or a low minimum temperature as a second component and a specific compound having a large dielectric anisotropy in the minor axis direction as a third component.

Claims

1. A liquid crystal composition for dimming, having a nematic phase and a positive dielectric anisotropy and including at least one compound represented by formula (1) as a first component: ##STR00035## in formula (1), R.sup.1 is alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons or alkenyl having 2 to 12 carbons; ring A is 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl or tetrahydropyran-2,5-diyl; Z.sup.1 is a single bond, ethylene, carbonyloxy or difluoromethyleneoxy; X.sup.1 and X.sup.2 are independently hydrogen or fluorine; Y.sup.1 is fluorine, chlorine, alkyl having 1 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine, alkoxy having 1 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine or alkenyloxy having 2 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine; and a is 1, 2, 3 or 4.

2. The liquid crystal composition for dimming according to claim 1, including at least one compound selected from the group of compounds represented by formula (1-1) to formula (1-35) as the first component: ##STR00036## ##STR00037## ##STR00038## in formula (1-1) to formula (1-35), R.sup.1 is alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons or alkenyl having 2 to 12 carbons.

3. The liquid crystal composition for dimming according to claim 1, wherein a proportion of the first component is in the range of 5% by mass to 90% by mass.

4. The liquid crystal composition for dimming according to claim 1, including at least one compound represented by formula (2) as a second component: ##STR00039## in formula (2), R.sup.2 and R.sup.3 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons or alkenyl having 2 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine; ring B and ring C are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene; Z.sup.2 is a single bond, ethylene or carbonyloxy; and b is 1, 2 or 3.

5. The liquid crystal composition for dimming according to claim 4, including at least one compound selected from the group of compounds represented by formula (2-1) to formula (2-13) as the second component: ##STR00040## ##STR00041## in formula (2-1) to formula (2-13), R.sup.2 and R.sup.3 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons or alkenyl having 2 to 12 carbons in which at least one hydrogen has been replaced by fluorine or chlorine.

6. The liquid crystal composition for dimming according to claim 4, wherein a proportion of the second component is in the range of 5% by mass to 90% by mass.

7. The liquid crystal composition for dimming according to claim 1, including at least one compound represented by formula (3) as a third component: ##STR00042## in formula (3), R.sup.4 and R.sup.5 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons or alkenyloxy having 2 to 12 carbons; ring D and ring F are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen has been replaced by fluorine or chlorine, naphthalene-2,6-diyl, naphthalene-2,6-diyl in which at least one hydrogen has been replaced by fluorine or chlorine, chromane-2,6-diyl or chromane-2,6-diyl in which at least one hydrogen has been replaced by fluorine or chlorine; ring E is 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 3,4,5-trifluoronaphthalene-2,6-diyl or 7,8-difluorochromane-2,6-diyl; Z.sup.3 and Z.sup.4 are independently a single bond, ethylene, carbonyloxy or methyleneoxy; c is 1, 2 or 3, and d is 0 or 1; and the sum of c and d is 3 or less.

8. The liquid crystal composition for dimming according to claim 7, including at least one compound selected from the group of compounds represented by formula (3-1) to formula (3-22) as the third component: ##STR00043## ##STR00044## ##STR00045## in formula (3-1) to formula (3-22), R.sup.4 and R.sup.5 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons or alkenyloxy having 2 to 12 carbons.

9. The liquid crystal composition for dimming according to claim 7, wherein a proportion of the third component is in the range of 3% by mass to 25% by mass.

10. The liquid crystal composition for dimming according to claim 1, wherein a maximum temperature of the nematic phase is 90 C. or higher.

11. A liquid crystal dimming device having a liquid crystal layer, wherein the liquid crystal layer is the liquid crystal composition for dimming according to claim 1.

12. The liquid crystal dimming device according to claim 11, wherein the liquid crystal layer is sandwiched between a pair of transparent substrates facing each other, the transparent substrate is a glass plate or an acrylic plate, the transparent substrate has a transparent electrode, and the transparent substrate may have an alignment layer.

13. The liquid crystal dimming device according to claim 11, wherein the liquid crystal layer is sandwiched between a pair of transparent substrates facing each other, the transparent substrate has a transparent electrode, the transparent substrate may have an alignment layer and the backside of one of the transparent substrates has a reflecting plate.

14. The liquid crystal dimming device according to claim 11, having a dimming material sandwiched between linear polarizers, wherein the dimming material has a laminated structure of a first film for a liquid crystal alignment layer, a liquid crystal layer and a second film for a liquid crystal alignment layer, and the first and second films for a liquid crystal alignment layer include a transparent plastic film substrate, a transparent electrode and an alignment layer.

15. A dimming window comprising the liquid crystal dimming device according to claim 11.

16. A smart window comprising the liquid crystal dimming device according to any one of claim 11.

17. (canceled)

18. (canceled)

19. (canceled)

20. (canceled)

21. A production method of a liquid crystal dimming device, including a step where a transparent electrode and an alignment layer are formed on at least one of a pair of transparent substrates; a step where the pair of transparent substrates is faced each other with the alignment layers inward; and a step where the liquid crystal composition for dimming according to claim 1 is filled between the pair of transparent substrates.

22. A production method of a liquid crystal dimming device, including a step where a transparent electrode and an alignment layer are formed on at least one of a pair of transparent substrates; a step where the pair of transparent substrates is faced each other with the alignment layers inward; and a step where the liquid crystal composition for dimming according to claim 1 is filled between the pair of transparent substrates, wherein the transparent substrates are plastic films.

23. A production method of a dimming window, including a step where a liquid crystal dimming device having the liquid crystal composition for dimming according to claim 1 is sandwiched between a pair of transparent substrates.

24. A production method of a smart window, including a step where a liquid crystal dimming device having the liquid crystal composition for dimming according to claim 1 is sandwiched between a pair of transparent substrates.

Description

EXAMPLES

[0070] The invention will be explained in more detail by way of examples. The invention is not limited to the examples. The invention includes a mixture of the composition in Example 1 and the composition in Example 2. The invention also includes a mixture prepared by mixing at least two compositions in Examples. Compounds prepared herein were identified by methods such as NMR analysis. The characteristics of the compounds, compositions and devices were measured by the methods described below.

[0071] NMR Analysis: A model DRX-500 apparatus made by Bruker BioSpin Corporation was used for measurement. In the measurement of .sup.1H-NMR, a sample was dissolved in a deuterated solvent such as CDCl.sub.3, and the measurement was carried out under the conditions of room temperature, 500 MHz and the accumulation of 16 scans. Tetramethylsilane was used as an internal standard. In the measurement of .sup.19F-NMR, CFCl.sub.3 was used as the internal standard, and 24 scans were accumulated. In the explanation of the nuclear magnetic resonance spectra, the symbols s, d, t, q, quin, sex, m and br stand for a singlet, a doublet, a triplet, a quartet, a quintet, a sextet, a multiplet and line-broadening, respectively.

[0072] Gas Chromatographic Analysis: A gas chromatograph Model GC-14B made by Shimadzu Corporation was used for measurement. The carrier gas was helium (2 milliliters per minute). The sample injector and the detector (FID) were set to 280 C. and 300 C., respectively. A capillary column DB-1 (length 30 meters, bore 0.32 millimeters, film thickness 0.25 micrometers, dimethylpolysiloxane as the stationary phase, non-polar) made by Agilent Technologies, Inc. was used for the separation of component compounds. After the column had been kept at 200 C. for 2 minutes, it was further heated to 280 C. at the rate of 5 C. per minute. A sample was dissolved in acetone (0.1% by mass), and 1 microliter of the solution was injected into the sample injector. A recorder used was Model C-R5A Chromatopac Integrator made by Shimadzu Corporation or its equivalent. The resulting gas chromatogram showed the retention time of peaks and the peak areas corresponding to the component compounds.

[0073] Solvents for diluting the sample may also be chloroform, hexane and so forth. The following capillary columns may also be used in order to separate the component compounds: HP-1 made by Agilent Technologies Inc. (length 30 meters, bore 0.32 millimeters, film thickness 0.25 micrometers), Rtx-1 made by Restek Corporation (length 30 meters, bore 0.32 millimeters, film thickness 0.25 micrometers), and BP-1 made by SGE International Pty. Ltd. (length 30 meters, bore 0.32 millimeters, film thickness 0.25 micrometers). A capillary column CBP1-M50-025 (length 50 meters, bore 0.25 millimeters, film thickness 0.25 micrometers) made by Shimadzu Corporation may also be used for the purpose of avoiding an overlap of peaks of the compounds.

[0074] The proportion of the liquid crystal compounds included in the composition may be calculated according to the following method. A mixture of the liquid crystal compounds was analyzed by gas chromatography (FID). The ratio of peak areas in the gas chromatogram corresponds to the proportion of the liquid crystal compounds. When the capillary columns described above are used, the correction coefficient of respective liquid crystal compounds may be regarded as 1 (one). Accordingly, the proportion (percentage by mass) of the liquid crystal compounds can be calculated from the ratio of peak areas.

[0075] Samples for measurement: A composition itself was used as a sample when the characteristics of the composition or the device were measured. When the characteristics of a compound were measured, a sample for measurement was prepared by mixing this compound (15% by mass) with mother liquid crystals (85% by mass). The characteristic values of the compound were calculated from the values obtained from measurements by an extrapolation method: (Extrapolated value)=(Measured value of sample)0.85(Measured value of mother liquid crystals)/0.15. When a smectic phase (or crystals) deposited at 25 C. at this proportion, the proportion of the compound to the mother liquid crystals was changed in the order of (10% by mass: 90% by mass), (5% by mass: 95% by mass) and (1% by mass: 99% by mass). The values of the maximum temperature, the optical anisotropy, the viscosity and the dielectric anisotropy regarding the compound were obtained by means of this extrapolation method.

[0076] The mother liquid crystals described below were used. The proportion of the component compounds was expressed as a percentage by mass.

##STR00018##

[0077] Measurement methods: The characteristics of compounds were measured according to the following methods. Most are methods described in the JEITA standards (JEITA-ED-2521B) which was deliberated and established by Japan Electronics and Information Technology Industries Association (abbreviated to JEITA), or the modified methods. No thin film transistors (TFT) were attached to a TN device used for measurement.

(1) Maximum Temperature of a Nematic Phase (NI; C.): A sample was placed on a hot plate in a melting point apparatus equipped with a polarizing microscope and was heated at the rate of 1 C. per minute. The temperature was measured when a part of the sample began to change from a nematic phase to an isotropic liquid. The maximum temperature of a nematic phase is sometimes abbreviated to the maximum temperature.
(2) Minimum Temperature of a Nematic Phase (Tc; C.): A sample having a nematic phase was placed in glass vials and then kept in freezers at temperatures of 0 C., 10 C., 20 C., 30 C. and 40 C. for 10 days, and then the liquid crystal phases were observed. For example, when the sample maintained the nematic phase at 20 C., and was changed to crystals or a smectic phase at 30 C., Tc was expressed as <20 C. The minimum temperature of a nematic phase is sometimes abbreviated to the minimum temperature.
(3) Viscosity (bulk viscosity; ; measured at 20 C.; mPa.Math.s): An E-type viscometer made by Tokyo Keiki Inc. was used for measurement.
(4) Viscosity (rotational viscosity; 1; measured at 25 C.; mPa.Math.s): The measurement was carried out according to the method described in M. Imai, et al., Molecular Crystals and Liquid Crystals, Vol. 259, 37 (1995). A sample was poured into a TN device in which the twist angle was 0 degrees and the distance between the two glass substrates (cell gap) was 5 micrometers. A voltage was applied to this device and increased stepwise with an increment of 0.5 volt in the range of 16 volts to 19.5 volts. After a period of 0.2 seconds with no voltage, a voltage was applied repeatedly under the conditions of a single rectangular wave alone (rectangular pulse; 0.2 seconds) and of no voltage (2 seconds). The peak current and the peak time of the transient current generated by the applied voltage were measured. The value of rotational viscosity was obtained from these measured values and the calculating equation (8) on page 40 of the paper presented by M. Imai, et al. The value of dielectric anisotropy necessary for this calculation was obtained by using the device that was used for measuring the rotational viscosity, by the method described below.
(5) Optical anisotropy (refractive index anisotropy; n; measured at 25 C.): The measurement was carried out using an Abbe refractometer with a polarizer attached to the ocular, using light at a wavelength of 589 nanometers. The surface of the main prism was rubbed in one direction, and then a sample was placed on the main prism. The refractive index (n) was measured when the direction of the polarized light was parallel to that of rubbing. The refractive index (n) was measured when the direction of polarized light was perpendicular to that of rubbing. The value of the optical anisotropy (n) was calculated from the equation: n=nn.
(6) Dielectric anisotropy (; measured at 25 C.): A sample was poured into a TN device in which the distance between the two glass substrates (cell gap) was 9 micrometers and the twist angle was 80 degrees. Sine waves (10 V, 1 kHz) were applied to this device, and the dielectric constant () in the major axis direction of liquid crystal molecules was measured after 2 seconds. Sine waves (0.5 V, 1 kHz) were applied to this device and the dielectric constant () in the minor axis direction of liquid crystal molecules was measured after 2 seconds. The value of dielectric anisotropy was calculated from the equation: =.
(7) Threshold voltage (Vth; measured at 25 C.; V): An LCD evaluation system Model LCD-5100 made by Otsuka Electronics Co., Ltd. was used for measurement. The light source was a halogen lamp. A sample was poured into a TN device having a normally white mode, in which the distance between the two glass substrates (cell gap) was 4.45/n (micrometers) and the twist angle was 80 degrees. A voltage to be applied to this device (32 Hz, rectangular waves) was stepwise increased in 0.02 V increments from 0 V up to 10 V. During the increase, the device was vertically irradiated with light, and the amount of light passing through the device was measured. A voltage-transmittance curve was prepared, in which the maximum amount of light corresponded to 100% transmittance and the minimum amount of light corresponded to 0% transmittance. The threshold voltage was expressed as voltage at 90% transmittance.
(8) Voltage Holding Ratio (VHR-1; measured at 25 C.; %): A TN device used for measurement had a polyimide-alignment film, and the distance between the two glass substrates (cell gap) was 5 micrometers. A sample was poured into the device, and then this device was sealed with a UV-curable adhesive. A pulse voltage (60 microseconds at 5 V) was applied to the TN device and the device was charged. A decreasing voltage was measured for 16.7 milliseconds with a high-speed voltmeter, and area A between the voltage curve and the horizontal axis in a unit cycle was obtained. Area B was an area without the decrease. The voltage holding ratio was expressed as a percentage of area A to area B.
(9) Voltage Holding Ratio (VHR-2; measured at 80 C.; %): The voltage holding ratio was measured by the method described above, except that it was measured at 80 C. instead of 25 C. The resulting values were represented by the symbol VHR-2.
(10) Voltage Holding Ratio (VHR-3; measured at 25 C.; %): The stability to ultraviolet light was evaluated by measuring a voltage holding ratio after irradiation with ultraviolet light. A TN device used for measurement had a polyimide-alignment film and the cell gap was 5 micrometers. A sample was poured into this device, and then the device was irradiated with light for 20 minutes. The light source was an ultra-high-pressure mercury lamp USH-500D (produced by Ushio, Inc.), and the distance between the device and the light source was 20 centimeters. In the measurement of VHR-3, a decreasing voltage was measured for 16.7 milliseconds. A composition having a large VHR-3 has a high stability to ultraviolet light. The VHR-3 is preferably 90% or more, and more preferably 95% or more.
(11) Voltage Holding Ratio (VHR-4; measured at 25 C.; %): A TN device into which a sample was poured was heated in a thermostatic oven at 80 C. for 500 hours, and then the stability to heat was evaluated by measuring the voltage holding ratio. In the measurement of VHR-4, a decreasing voltage was measured for 16.7 milliseconds. A composition having a large VHR-4 has a high stability to heat.
(12) Response Time (; measured at 25 C.; ms): An LCD evaluation system Model LCD-5100 made by Otsuka Electronics Co., Ltd. was used for measurement. The light source was a halogen lamp. The low-pass filter was set at 5 kHz. A sample was poured into a TN device having a normally white mode, in which the distance between the two glass substrates (cell gap) was 5.0 micrometers and the twist angle was 80 degrees. Rectangular waves (60 Hz, 5 V, 0.5 second) were applied to this device. The device was vertically irradiated with light simultaneously, and the amount of light passing through the device was measured. The transmittance was regarded as 100% when the amount of light reached a maximum. The transmittance was regarded as 0% when the amount of light reached a minimum. Rise time (r; millisecond) was the time required for a change from 90% to 10% transmittance. Fall time (f; millisecond) was the time required for a change from 10% to 90% transmittance. The response time was expressed as the sum of the rise time and the fall time thus obtained.
(13) Elastic constants (K; measured at 25 C.; pN): A LCR meter Model HP 4284-A made by Yokokawa Hewlett-Packard, Ltd. was used for measurement. A sample was poured into a homogeneous device in which the distance between the two glass substrates (cell gap) was 20 micrometers. An electric charge of 0 volts to 20 volts was applied to this device, and the electrostatic capacity and the applied voltage were measured. The measured values of the electric capacity (C) and the applied voltage (V) were fitted to equation (2.98) and equation (2.101) on page 75 of Ekisho Debaisu Handobukku (Liquid Crystal Device Handbook, in English; The Nikkan Kogyo Shimbun, Ltd., Japan) and the values of K11 and K33 were obtained from equation (2.99). Next, K22 was calculated by plugging the values of K11 and K33 obtained into equation (3.18) on page 171 of the book. The elastic constant K was expressed as an average value of K11, K22 and K33.
(14) Specific Resistance (; measured at 25 C.; cm): A sample (1.0 mL) was placed in a vessel equipped with electrodes. A DC voltage (10 V) was applied to this vessel, and the DC current was measured after 10 seconds. The specific resistance was calculated from the following equation:

(specific resistance)=[(voltage)(electric capacity of vessel)]/[(DC current)(dielectric constant in vacuum)]. (equation 1)

(15) Helical pitch (P; measured at room temperature; micrometer): The helical pitch was measured according to the wedge method (see page 196 of Ekishou Binran (Liquid Crystal Handbook, in English; Maruzen, Co., LTD., Japan, 2000). After a sample had been injected into a wedge-shaped cell and the cell had been allowed to stand at room temperature for 2 hours, the distance (d2d1) between disinclination lines was observed with a polarizing microscope (Nikon Corporation, Model MM-40/60 series). The helical pitch (P) was calculated from the following equation, wherein was defined as the angle of the wedge cell: P=2(d2d1)tan .
(16) Dielectric constant in the minor axis direction (; measured at 25 C.): A sample was poured into a TN device in which the distance between the two glass substrates (cell gap) was 9 micrometers and the twist angle was 80 degrees. Sine waves (0.5 V, 1 kHz) were applied to this device and the dielectric constant () in the minor axis direction of liquid crystal molecules was measured after 2 seconds.
(17) Alignment stability (Stability of liquid crystal alignment axis): In an FFS device, the change of a liquid crystal alignment axis in a side of electrode was evaluated. A liquid crystal alignment angle [(before)] before stressed in the side of an electrode was measured. Rectangular waves (4.5V, 60 Hz) were applied for 20 minutes to the device, the device was short circuited for 1 second, and then a liquid crystal alignment angle [(after)] in the side of the electrode was measured after 1 second and 5 minutes. The change (, deg.) of the liquid crystal alignment angle after 1 second and 5 minutes was calculated from these values by the following equation:

(deg.)=(after)(before)(equation 2)

These measurements were carried out by referring J. Hilfiker, B. Johs, C. Herzinger, J. F. Elman, E. Montbach, D. Bryant and P. J. Bos, Thin Solid Films, 455-456, (2004) 596-600. The smaller value of means a smaller change ratio of the liquid crystal alignment axis, which means that the stability of liquid crystal alignment axis is better.
(18) Flicker rate (measured at 25 C.; %): A multimedia display tester 3298F made by Yokogawa Electric Corporation was used for measurement. The light source was LED. A sample was poured into a device having a normally black mode, in which the distance between the two glass substrates (cell gap) was 3.5 micrometers and the rubbing direction was antiparallel. This device was sealed with a UV-curable adhesive. A voltage was applied to the device and a voltage was measured when the amount of light passed through the device reached a maximum. The sensor was brought close to the device while this voltage was applied to the device, and the flicker rate displayed was recorded.
(19) Haze (%): A haze meter HZ-V3 (made by Suga Test Instruments Co., Ltd.) or the like can be used for measuring haze.

[0078] Examples of compositions will be shown below. Component compounds were expressed in terms of symbols according to the definition in Table 3 described below. In Table 3, the configuration of 1,4-cyclohexylene is trans. The parenthesized number next to a symbolized compound represents the chemical formula to which the compound belongs. The symbol (-) means any other liquid crystal compound. The proportion (percentage) of a liquid crystal compound means the percentages by mass (% by mass) based on the mass of the liquid crystal composition excluding additives. Last, the values of characteristics of the composition are summarized.

TABLE-US-00003 TABLE 3 Method of description of compounds using symbols R-(A.sub.1)-Z.sub.1- . . . -Z.sub.n-(A.sub.n)-R 1) Left-terminal Group R- Symbol C.sub.nH.sub.2n+1 n- C.sub.nH.sub.2n+1O nO- C.sub.mH.sub.2m+1OC.sub.nH.sub.2n mOn- CH.sub.2CH V- C.sub.nH.sub.2n+1CHCH nV- CH.sub.2CHC.sub.nH.sub.2n Vn- C.sub.mH.sub.2m+1CHCHC.sub.nH.sub.2n mVn- CF.sub.2CH VFF- CF.sub.2CHC.sub.nH.sub.2n VFFn- FC.sub.nH.sub.2n Fn- 2) Right-terminal Group -R Symbol C.sub.nH.sub.2n+1 -n OC.sub.nH.sub.2n+1 -On CHCH.sub.2 -V CHCHC.sub.nH.sub.2n+1 -Vn C.sub.nH.sub.2nCHCH.sub.2 -nV C.sub.mH.sub.2mCHCHC.sub.nH.sub.2n+1 -mVn CHCF.sub.2 -VFF COOCH.sub.3 -EMe F F Cl -CL OCF.sub.3 OCF.sub.3 CF.sub.3 CF.sub.3 CN C 3) Bonding Group Z.sub.n Symbol C.sub.nH.sub.2n n COO E CHCH V CC T CF.sub.2O X CH.sub.2O 1O 4) Ring Structure -A.sub.n Symbol [00019] H [00020] dh [00021] Dh [00022] B [00023] B(F) [00024] B(2F) [00025] B(F,F) [00026] B(2F,5F) [00027] G [00028] Py [00029] B(2F,3F) 5) Examples of Description Example 1. 3-HH-V [00030] Example 2. 3-HHB(2F,3F)-O2 [00031] Example 3. 4-GB(F)B(F,F)XB(F,F)-F [00032] Example 4. 2-BB(F)B(F,F)-F [00033]

Example 1

[0079]

TABLE-US-00004 5-HXB(F,F)-F (1-1) 3% 3-HHXB(F,F)-F (1-4) 5% 3-HGB(F,F)-F (1-6) 3% 3-HB(F)B(F,F)-F (1-9) 5% 3-BB(F,F)XB(F,F)-F (1-18) 4% 3-HHBB(F,F)-F (1-19) 5% 4-HHBB(F,F)-F (1-19) 4% 3-GBB(F)B(F,F)-F (1-22) 3% 4-GBB(F)B(F,F)-F (1-22) 3% 5-BB(F)B(F,F)XB(F)B(F,F)-F (1-31) 3% 3-BB(2F,3F)XB(F,F)-F (1-32) 3% 3-HB-CL (1) 3% 3-HHB-OCF3 (1) 3% 3-HH2BB(F,F)-F (1) 3% 3-HHB(F,F)XB(F,F)-F (1) 3% 3-HBB(2F,3F)XB(F,F)-F (1) 4% 3-HH-V (2-1) 20% 3-HH-V1 (2-1) 7% 5-HB-O2 (2-2) 3% 3-HHEH-3 (2-4) 3% 3-HBB-2 (2-6) 7% 5-B(F)BB-3 (2-7) 3% NI = 92.7 C.; Tc < 20 C.; n = 0.114; = 6.9; Vth = 1.53 V; = 24.8 mPa .Math. s.

Example 2

[0080]

TABLE-US-00005 5-HXB(F,F)-F (1-1) 4% 3-HHXB(F,F)-F (1-4) 5% 3-HB(F)B(F,F)-F (1-9) 3% V-HB(F)B(F,F)-F (1-9) 3% 2-HHB(F)B(F,F)-F (1-20) 3% 3-HHB(F)B(F,F)-F (1-20) 5% 3-GBB(F)B(F,F)-F (1-22) 3% 4-GBB(F)B(F,F)-F (1-22) 3% 2-BB(F)B(F,F)XB(F)-F (1-28) 3% 3-BB(F)B(F,F)XB(F)-F (1-28) 3% 4-BB(F)B(F,F)XB(F)-F (1-28) 3% 5-BB(F)B(F,F)XB(F,F)-F (1-29) 3% 5-HB-CL (1) 3% 3-dhB(F,F)B(F,F)XB(F)B(F,F)-F (1) 3% 2-HH-5 (2-1) 6% 3-HH-V (2-1) 9% 3-HH-V1 (2-1) 5% 4-HH-V (2-1) 8% 4-HH-V1 (2-1) 6% 5-HB-O2 (2-2) 5% 3-HHEH-3 (2-4) 3% 4-HHEH-3 (2-4) 3% V2-BB(F)B-1 (2-8) 3% 1O1-HBBH-3 () 5% NI = 94.0 C.; Tc < 20 C.; n = 0.114; = 6.9; Vth = 1.54 V; = 23.5 mPa .Math. s.

Example 3

[0081]

TABLE-US-00006 3-HHEB(F,F)-F (1-3) 5% 3-HHXB(F,F)-F (1-4) 7% 5-HBEB(F,F)-F (1-10) 5% 3-BB(F,F)XB(F,F)-F (1-18) 10% 2-HHB(F)B(F,F)-F (1-20) 3% 5-HHB(F,F)XB(F,F)-F (1) 6% 3-HBB(2F,3F)XB(F,F)-F (1) 5% 2-HH-3 (2-1) 8% 3-HH-V (2-1) 20% 3-HH-V1 (2-1) 7% 4-HH-V (2-1) 6% 5-HB-O2 (2-2) 5% V2-B2BB-1 (2-9) 3% 3-HHEBH-3 (2-11) 5% 3-HHEBH-5 (2-11) 5% NI = 90.3 C.; Tc < 20 C.; n = 0.088; = 5.4; Vth = 1.69 V; = 13.7 mPa .Math. s.

Example 4

[0082]

TABLE-US-00007 3-BB(F,F)XB(F,F)-F (1-18) 9% 3-HHBB(F,F)-F (1-19) 5% 4-HHBB(F,F)-F (1-19) 4% 3-HBBXB(F,F)-F (1-23) 3% 3-BB(F)B(F,F)XB(F)-F (1-28) 3% 4-BB(F)B(F,F)XB(F)-F (1-28) 3% 3-BB(F)B(F,F)XB(F,F)-F (1-29) 3% 5-BB(F)B(F,F)XB(F,F)-F (1-29) 3% 3-HHB(F,F)XB(F,F)-F (1) 3% 5-HHB(F,F)XB(F,F)-F (1) 3% 2-HH-3 (2-1) 5% 3-HH-5 (2-1) 5% 3-HH-V (2-1) 20% 3-HH-VFF (2-1) 5% 5-HB-O2 (2-2) 6% 3-HHB-1 (2-5) 3% 3-HHB-3 (2-5) 3% V-HHB-1 (2-5) 6% V-HBB-2 (2-6) 6% 3-HHEBH-4 (2-11) 2% NI = 94.5 C.; Tc < 20 C.; n = 0.111; = 6.8; Vth = 1.55 V; = 16.6 mPa .Math. s.

Example 5

[0083]

TABLE-US-00008 3-HHXB(F,F)-F (1-4) 7% 3-BB(F,F)XB(F,F)-F (1-18) 5% 3-HHBB(F,F)-F (1-19) 6% 4-HHBB (F,F)-F (1-19) 5% 4-BB(F)B(F,F)XB(F)-F (1-28) 5% 3-BB(F)B(F,F)XB(F,F)-F (1-29) 4% 5-BB(F)B(F,F)XB(F,F)-F (1-29) 4% 3-HHB-OCF3 (1) 5% 3-HH-V (2-1) 27% 3-HH-V1 (2-1) 4% F3-HH-V (2-1) 10% 1V2-HH-3 (2-1) 5% 3-HHB-O1 (2-5) 2% V-HHB-1 (2-5) 5% 2-BB(F)B-3 (2-8) 6% NI = 91.8 C.; Tc < 20 C.; n = 0.107; = 5.4; Vth = 1.71 V; = 13.2 mPa .Math. s.

Example 6

[0084]

TABLE-US-00009 3-HGB(F,F)-F (1-6) 4% 5-GHB(F,F)-F (1-7) 3% 3-GB(F,F)XB(F,F)-F (1-14) 3% 3-HHBB(F,F)-F (1-19) 4% 4-HHBB(F,F)-F (1-19) 3% 2-HHB(F)B(F,F)-F (1-20) 4% 3-GBB(F)B(F,F)-F (1-22) 3% 4-GBB(F)B(F,F)-F (1-22) 4% 2-dhBB(F,F)XB(F,F)-F (1-25) 3% 7-HB(F,F)-F (1) 3% 3-HGB(F,F)XB(F,F)-F (1) 3% 3-dhB(F,F)B(F,F)XB(F)B(F,F)-F (1) 3% 2-HH-3 (2-1) 10% 2-HH-5 (2-1) 3% 3-HH-V (2-1) 26% 1V2-HH-3 (2-1) 4% 1V2-BB-1 (2-3) 3% 3-HB(F)HH-2 (2-10) 4% 5-HBB(F)B-2 (2-13) 5% 3-BB(2F,5F)B-3 (2) 5% NI = 91.5 C.; Tc < 20 C.; n = 0.106; = 5.8; Vth = 1.61 V; = 21.1 mPa .Math. s.

Example 7

[0085]

TABLE-US-00010 3-HBB(F,F)-F (1-8) 4% 5-HBB(F,F)-F (1-8) 3% 3-BB(F)B(F,F)-F (1-15) 4% 2-dhBB(F,F)XB(F,F)-F (1-25) 3% 2-BB(F)B(F,F)XB(F)-F (1-28) 5% 4-BB(F)B(F,F)XB(F)-F (1-28) 3% 3-BB(F)B(F,F)XB(F,F)-F (1-29) 3% 3-BB(F,F)XB(F)B(F,F)-F (1-30) 3% 5-BB(F)B(F,F)XB(F)B(F,F)-F (1-31) 3% 3-HH2BB(F,F)-F (1) 3% 4-HH2BB(F,F)-F (1) 3% 3-HGB(F,F)XB(F,F)-F (1) 3% 3-HBB(2F,3F)XB(F,F)-F (1) 3% 2-HH-5 (2-1) 5% 3-HH-V (2-1) 23% 3-HH-V1 (2-1) 3% 4-HH-V1 (2-1) 4% 5-HB-O2 (2-2) 3% 7-HB-1 (2-2) 3% VFF-HHB-1 (2-5) 3% VFF-HHB-O1 (2-5) 8% 5-HBB(F)B-2 (2-13) 5% NI = 94.3 C.; Tc < 20 C.; n = 0.122; = 7.7; Vth = 1.45 V; = 23.0 mPa .Math. s.

Example 8

[0086]

TABLE-US-00011 3-HHB(F,F)-F (1-2) 8% 3-GB(F)B(F,F)-F (1-12) 3% 3-BB(F,F)XB(F,F)-F (1-18) 8% 3-HHBB(F,F)-F (1-19) 5% 3-GB(F)B(F,F)XB(F,F)-F (1-27) 5% 5-GB(F,F)XB(F)B(F,F)-F (1) 3% 3-HH-V (2-1) 25% 3-HH-V1 (2-1) 8% 3-HH-VFF (2-1) 6% 1V2-HH-3 (2-1) 8% V2-BB-1 (2-3) 2% 3-HHB-3 (2-5) 4% V-HHB-1 (2-5) 5% 5-HB(F)BH-3 (2-12) 5% 5-HBBH-3 (2) 5% NI = 92.4 C.; Tc < 20 C.; n = 0.096; = 4.6; Vth = 1.80 V; = 16.2 mPa .Math. s.

Example 9

[0087]

TABLE-US-00012 3-HHEB(F,F)-F (1-3) 6% 3-HBEB(F,F)-F (1-10) 3% 5-HBEB(F,F)-F (1-10) 3% 3-BB(F)B(F,F)-F (1-15) 3% 4-HHBB(F,F)-F (1-19) 5% 3-HHB(F)B(F,F)-F (1-20) 3% 3-GBB(F)B(F,F)-F (1-22) 3% 3-GB(F)B(F,F)XB(F,F)-F (1-27) 4% 4-GB(F)B(F,F)XB(F,F)-F (1-27) 3% 5-HB-CL (1) 4% 3-HHB-OCF3 (1) 5% 5-HEB(F,F)-F (1) 3% 3-HHB(F,F)XB(F,F)-F (1) 3% 5-HHB(F,F)XB(F,F)-F (1) 3% 3-HGB(F,F)XB(F,F)-F (1) 3% 2-HH-5 (2-1) 3% 3-HH-5 (2-1) 4% 3-HH-V (2-1) 20% 4-HH-V (2-1) 4% 1V2-HH-3 (2-1) 3% 3-HHEH-3 (2-4) 5% 5-B(F)BB-2 (2-7) 5% 5-B(F)BB-3 (2-7) 2% NI = 91.2 C.; Tc < 20 C.; n = 0.104; = 6.8; Vth = 1.54 V; = 23.0 mPa .Math. s.

Example 10

[0088]

TABLE-US-00013 3-HHXB(F,F)-F (1-4) 7% 5-HBB(F,F)-F (1-8) 3% 3-BB(F)B(F,F)-F (1-15) 4% 3-BB(F)B(F,F)-CF3 (1-16) 4% 3-BB(F,F)XB(F,F)-F (1-18) 3% 3-GBB(F)B(F,F)-F (1-22) 3% 4-GBB(F)B(F,F)-F (1-22) 4% 3-BB(F)B(F,F)XB(F,F)-F (1-29) 4% 5-BB(F)B(F,F)XB(F,F)-F (1-29) 3% 3-HH-V (2-1) 22% 3-HH-V1 (2-1) 6% 5-HB-O2 (2-2) 9% 7-HB-1 (2-2) 4% V2-BB-1 (2-3) 3% 3-HHB-1 (2-5) 4% V-HHB-1 (2-5) 3% 1V-HBB-2 (2-6) 5% 5-HB(F)BH-3 (2-12) 3% 5-HBB(F)B-2 (2-13) 6% NI = 91.1 C.; Tc < 20 C.; n = 0.126; = 6.3; Vth = 1.60 V; = 17.4 mPa .Math. s.

Example 11

[0089]

TABLE-US-00014 3-HHEB(F,F)-F (1-3) 5% 5-HBEB(F,F)-F (1-10) 3% 3-BB(F,F)XB(F,F)-F (1-18) 10% 3-HHBB(F,F)-F (1-19) 3% 4-HHBB(F,F)-F (1-19) 3% 7-HB(F,F)-F (1) 4% 3-dhB(F,F)B(F,F)XB(F)B(F,F)-F (1) 5% 2-HH-5 (2-1) 5% 3-HH-V (2-1) 25% 3-HH-V1 (2-1) 3% 3-HH-VFF (2-1) 8% 3-HHB-1 (2-5) 5% 3-HHB-3 (2-5) 5% 3-HHB-O1 (2-5) 4% 3-HHEBH-3 (2-11) 3% 3-HHEBH-4 (2-11) 3% 3-HHEBH-5 (2-11) 3% 3-BB(2F,5F)B-3 (2) 3% NI = 97.7 C.; Tc < 20 C.; n = 0.092; = 4.7; Vth = 1.77 V; = 14.4 mPa .Math. s.

Example 12

[0090]

TABLE-US-00015 3-HBB(F,F)-F (1-8) 3% 5-HBB(F,F)-F (1-8) 3% 4-BB(F)B(F,F)XB(F)-F (1-28) 5% 3-BB(F)B(F,F)XB(F,F)-F (1-29) 3% 3-BB(F,F)XB(F)B(F,F)-F (1-30) 3% 5-BB(F)B(F,F)XB(F)B(F,F)-F (1-31) 4% 3-HH2BB(F,F)-F (1) 3% 4-HH2BB(F,F)-F (1) 4% 2-HH-5 (2-1) 8% 3-HH-V (2-1) 27% 4-HH-V1 (2-1) 6% 5-HB-O2 (2-2) 2% 7-HB-1 (2-2) 3% 3-HHB-1 (2-5) 3% VFF-HHB-1 (2-5) 3% VFF-HHB-O1 (2-5) 8% V-HBB-2 (2-6) 5% 2-BB(2F,3F)B-3 (3-9) 4% 3-HBB(2F,3F)-O2 (3-10) 3% NI = 92.7 C.; Tc < 20 C.; n = 0.114; = 4.3; Vth = 1.80 V; = 13.8 mPa .Math. s.

Example 13

[0091]

TABLE-US-00016 3-HHEB(F,F)-F (1-3) 4% 3-HBEB(F,F)-F (1-10) 3% 5-HBEB(F,F)-F (1-10) 3% 3-BB(F)B(F,F)-F (1-15) 3% 3-HHBB(F,F)-F (1-19) 4% 4-HHBB(F,F)-F (1-19) 5% 3-HBBXB(F,F)-F (1-23) 6% 3-GB(F)B(F,F)XB(F,F)-F (1-27) 4% 4-GB(F)B(F,F)XB(F,F)-F (1-27) 4% 5-HB-CL (1) 2% 3-HHB-OCF3 (1) 4% 5-HEB(F,F)-F (1) 3% 5-HHB(F,F)XB(F,F)-F (1) 4% 3-HGB(F,F)XB(F,F)-F (1) 5% 3-HH-5 (2-1) 3% 3-HH-V (2-1) 15% 3-HH-V1 (2-1) 3% 4-HH-V (2-1) 3% F3-HH-V (2-1) 3% 1V2-HH-3 (2-1) 3% 5-B(F)BB-2 (2-7) 5% 5-B(F)BB-3 (2-7) 2% 3-HB(2F,3F)-O2 (3-1) 3% 3-BB(2F,3F)-O2 (3-4) 2% 3-HHB(2F,3F)-O2 (3-6) 4% NI = 90.9 C.; Tc < 20 C.; n = 0.112; = 7.5; Vth = 1.48 V; = 25.5 mPa .Math. s.

Example 14

[0092]

TABLE-US-00017 2-HHB(F,F)-F (1-2) 6% 3-HHB(F,F)-F (1-2) 6% 3-HBB(F,F)-F (1-8) 18% 2-HHBB(F,F)-F (1-19) 4% 3-HHBB(F,F)-F (1-19) 4% 4-HHBB(F,F)-F (1-19) 3% 5-HHBB(F,F)-F (1-19) 2% 3-HHB-F (1) 4% 2-HHB(F)-F (1) 6% 3-HHB(F)-F (1) 7% 5-HHB(F)-F (1) 6% 3-HH-4 (2-1) 10% 3-HB-O2 (2-2) 8% 5-HB-O2 (2-2) 8% 3-HHB-1 (2-5) 5% 3-HHB-O1 (2-5) 3% NI = 101.9 C.; Tc < 40 C.; n = 0.098; = 5.2; Vth = 1.85 V; = 21.7 mPa .Math. s.

Example 15

[0093]

TABLE-US-00018 2-HHB(F,F)-F (1-2) 7% 3-HHB(F,F)-F (1-2) 7% 3-HBB(F,F)-F (1-8) 4% 2-HHBB(F,F)-F (1-19) 4% 3-HHBB(F,F)-F (1-19) 4% 4-HHBB(F,F)-F (1-19) 4% 5-HHBB(F,F)-F (1-19) 4% 3-HHB-F (1) 4% 2-HHB(F)-F (1) 6% 3-HHB(F)-F (1) 7% 5-HHB(F)-F (1) 6% 3-H2HB(F,F)-F (1) 7% 5-H2HB(F,F)-F (1) 7% 5-HB-O2 (2-2) 7% 7-HB-1 (2-2) 15% 3-HHB-1 (2-5) 4% 3-HHB-O1 (2-5) 3% NI = 98.8 C.; Tc < 40 C.; n = 0.088; = 5.0; Vth = 1.83 V; = 24.7 mPa .Math. s.

Example 16

[0094] The following optically active compound (4-5) was added to the composition described in Example 15 in the proportion of 0.2% by mass.

##STR00034##

Production of the Liquid Crystal Dimming Device

[0095] The liquid crystal dimming device having a dimming material sandwiched between linear polarizers is produced. The dimming material has a laminated structure of a first polycarbonate film, a liquid crystal layer and a second polycarbonate film. The first and second polycarbonate films are transparent, and have a transparent electrode and an alignment layer. The liquid crystal layer is filled with a liquid crystal composition including at least one compound selected from the group of compounds represented by formula (1) as a first component and having positive dielectric anisotropy.

[0096] When the characteristics of the liquid crystal composition or the liquid crystal display device are measured, a device having a glass substrate is usually used. In the liquid crystal dimming device, a plastic film is sometimes used as a substrate. Then, a device in which the substrate was polycarbonate was produced and the characteristics such as a threshold voltage and a response time were measured. The measured value was compared with these of a device having a glass plate. As a result, two types of measured values were almost the same. Thus, the substrate can be regarded as carbonate even if a glass substrate is used, when the characteristics of the liquid crystal composition or the liquid crystal dimming device are measured. Here, measurement using a device having a glass substrate was described with regard to characteristics such as a threshold voltage and a response time.

INDUSTRIAL APPLICABILITY

[0097] The liquid crystal dimming device including a liquid crystal composition for dimming of the invention can be used for dimming windows or smart windows, since it has characteristics such as a large voltage holding ratio, a low threshold voltage, a large contrast ratio and a long service life.